O'Neil Property Group

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$2,100,000
5 Days On Site

285 Woodlawn Avenue
Winnetka, IL 60093

For Sale|Single Family Residence|Active
4
Beds
6
Total Baths
5
Full Baths
1
Partial Bath
3,697
SqFt
$568
/SqFt
2007
Built
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of Baird & Warner
285 Woodlawn Avenue285 Woodlawn Avenue285 Woodlawn Avenue285 Woodlawn Avenue
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Welcome to this exquisite, sun-drenched 4+1 bed, 5.1 bath luxury home on an oversized lot (50x232) at the Winnetka/Glencoe border. Located on a beautiful tree lined cul-de-sac and adjacent to the Green Bay trail, this home sits across the street from Glencoe Park. The moment you walk in, you are greeted by a bright formal living room featuring one of the home's four fireplaces, flanked by an adjacent office adorned with beautiful, oversized bay windows. Designed for seamless modern living, the main level flows into a sophisticated formal dining room, an open-concept kitchen, breakfast room and family room overlooking expansive backyard. The main level features a light, neutral palette and newer light fixtures throughout. The second floor is a private retreat where all four bedrooms feature dedicated en suite baths, and two enjoy the luxury of private decks. All new hardwood flooring throughout this level along with a fresh paint. Spacious primary bedroom features large walk in closet and elegantly renovated bathroom with double vanity and a breathtaking walk in shower. A dedicated second-floor laundry room includes a newer washer/dryer. Fully finished basement adds incredible value with a huge recreation room, a full bath, bar and a flexible 5th bedroom/home gym. Enjoy cozy evenings anchored by the home's 4 distinct fireplaces. The outdoor oasis features an oversized paver patio, massive yard, and an oversized 2-car garage. Impeccably maintained with newer appliances, wine cooler, updated mechanicals, and a central vac system, this home offers total peace of mind. Unbeatable location just minutes from Hubbard Woods shopping, dining, and the Metra train.

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Listing Snapshot
PriceΒ 
$2,100,000
Days On SiteΒ 
5 Days
BedroomsΒ 
4
Inside Area (SqFt)Β 
3,697 sqft
Total BathsΒ 
6
Full BathsΒ 
5
Partial BathsΒ 
1
Lot SizeΒ 
0.26 Acres
Year BuiltΒ 
2007
MLS NumberΒ 
12798477
StatusΒ 
Active
Property TaxΒ 
$41,577.8
HOA/Condo/Coop FeesΒ 
N/A
Sq Ft SourceΒ 
Estimated
Friends & Family
Recent Activity
2 hours agoListing updated with changes from the MLS
2 hours agoStatus changed to Active
6 days agoListing first seen on site
General Features
AcresΒ 
0.26
FoundationΒ 
Concrete Perimeter
GarageΒ 
Yes
Garage SpacesΒ 
2
ParkingΒ 
AsphaltDetachedGarage
Parking SpacesΒ 
2
Property Sub TypeΒ 
Single Family Residence
SecurityΒ 
Security System
SewerΒ 
Public Sewer
SqFt BelowΒ 
1655
SqFt TotalΒ 
3697
StyleΒ 
Other
UtilitiesΒ 
Cable Available
Water SourceΒ 
Public
Interior Features
AppliancesΒ 
RangeMicrowaveDishwasherRefrigeratorBar FridgeWasherDryerDisposal
BasementΒ 
Sump PumpFinishedFull
CoolingΒ 
Ceiling Fan(s)Central AirZoned
ElectricΒ 
Circuit Breakers200+ Amp Service
FireplaceΒ 
Yes
Fireplace FeaturesΒ 
Family RoomLiving RoomMaster Bedroom
FireplacesΒ 
4
HeatingΒ 
Forced AirRadiantZoned
InteriorΒ 
Entrance FoyerSaunaWet Bar
SpaΒ 
Yes
Bedroom 2Β 
Dimensions - 14X12Level - Second
Bedroom 3Β 
Dimensions - 14X19Level - Second
Bedroom 4Β 
Dimensions - 14X16Level - Second
Bedroom 5Β 
Dimensions - 15X13Level - Basement
Breakfast RoomΒ 
Dimensions - 10X8Level - Main
Dining RoomΒ 
Dimensions - 14X14Level - Main
Family RoomΒ 
Dimensions - 24X16Level - Main
FoyerΒ 
Dimensions - 14X6Level - Main
KitchenΒ 
Dimensions - 21X13Level - MainDescription - Eating Area-Breakfast Bar,Eating Area-Table Space,Island,Pantry-Butler,Pantry-Closet,Pantry-Walk-in
LaundryΒ 
Dimensions - 7X6Level - Second
Living RoomΒ 
Dimensions - 21X14Level - Main
Master BedroomΒ 
Dimensions - 19X15Level - Second
OfficeΒ 
Dimensions - 16X13Level - Main
Recreation RmΒ 
Dimensions - 50X24Level - Basement
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Exterior Features
Construction DetailsΒ 
CedarStone
ExteriorΒ 
Balcony
FencingΒ 
Fenced
Lot FeaturesΒ 
Cul-De-SacLandscapedWooded
Patio And PorchΒ 
Patio
RoofΒ 
Asphalt
SpaΒ 
Yes
Community Features
Accessibility FeaturesΒ 
Therapeutic Whirlpool
Community FeaturesΒ 
ParkTennis Court(s)CurbsSidewalksStreet Lights
MLS AreaΒ 
Winnetka
School DistrictΒ 
New Trier Twp H.S. Northfield/Wi
TownshipΒ 
New Trier
Schools
School District
New Trier Twp H.S. Northfield/Wi
Elementary School
South Elementary School
Middle School
Central School
High School
New Trier Twp H.S. Northfield/Wi
Listing Courtesy of MRED as distributed by MLS Grid of Baird & Warner



Based on information submitted to the MLS GRID as of 2026-11-09 08:19 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last checked: 2026-11-09 08:19 AM UTC
MRED DMCA Copyright Information Copyright Β© 2026 Midwest Real Estate Data LLC. All rights reserved.

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